Benzene → HCID 56634238, compound

HRID 2309076Notes

Reaction equation

HRID 2309076 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]([N:8]1[C@@H:11]([S:12]SC2SC3C=CC=CC=3N=2)[C@@H:10]([O:23][CH3:24])[C:9]1=[O:25])=[C:5]([CH3:7])[CH3:6].[BH4-].[Na+].[C:29](Br)(=[O:31])[CH3:30].C1C=CC=CC=1>CN(C)C=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[C:4]([N:8]1[C@H:11]([S:12][C:29](=[O:31])[CH3:30])[C@@H:10]([O:23][CH3:24])[C:9]1=[O:25])=[C:5]([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 241BenzeneHCID 10482Acetyl bromideHCID 4311764Sodium borohydrideHCID 57193146HCID 57193146, compound

Product 1

HCID 56634238HCID 56634238, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21584019Toluene ethylacetateSolvent

Procedure

A solution of 372 mg of 2-[(3S,4S)-4-(benzthiazol-2-yldithio)-3-methoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid methyl ester in 10 ml of dimethylformamide is cooled to -20°, 10 ml of a solution of 2 g of sodium borohydride in 200 ml of dimethylformamide are added and the mixture is stirred at the same temperature for 30 minutes. 5 ml of freshly distilled acetyl bromide are added to the reaction mixture and the mixture is further stirred for 110 minutes at 0°. After adding 150 ml of benzene, the reaction mixture is washed in successsion with sodium bicarbonate solution and water, dried over sodium sulphate and concentrated by evaporation in vacuo. The residue yields, after chromatography over silica gel with toluene/ethyl acetate (9:1), the title compound in the form of a slightly yellowish oil.

Workup

  1. stirringthe mixture is further stirred for 110 minutes at 0°
  2. washthe reaction mixture is washed in successsion with sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue yields

Sources & evidence

ORD record
ord-c021a2d8e57a4acba906a029b78405ea
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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